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> Main
CHEBI:61338 - bacillithiol
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ChEBI Name
bacillithiol
ChEBI ID
CHEBI:61338
Definition
A thiol that is the α-anomeric glycoside of
L
-cysteinyl-
D
-glucosamine with
L
-malic acid.
Stars
This entity has been manually annotated by the ChEBI Team.
Submitter
Midori Harris
Supplier Information
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Formula
C13H22N2O10S
Net Charge
0
Average Mass
398.38600
Monoisotopic Mass
398.09952
InChI
InChI=1S/C13H22N2O10S/c14-
4(3-
26)
11(21)
15-
8-
10(20)
9(19)
6(2-
16)
25-
13(8)
24-
5(12(22)
23)
1-
7(17)
18/h4-
6,8-
10,13,16,19-
20,26H,1-
3,14H2,(H,15,21)
(H,17,18)
(H,22,23)
/t4-
,5-
,6+,8+,9+,10+,13-
/m0/s1
InChIKey
UHNHELGKNQMNGF-AOQKXWSCSA-N
SMILES
N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H](CC(O)=O)C(O)=O
Roles Classification
Chemical Role
(s):
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role
(s):
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
bacillithiol (
CHEBI:61338
)
has role
antioxidant (
CHEBI:22586
)
bacillithiol (
CHEBI:61338
)
has role
bacterial metabolite (
CHEBI:76969
)
bacillithiol (
CHEBI:61338
)
has role
cofactor (
CHEBI:23357
)
bacillithiol (
CHEBI:61338
)
is a
glycoside (
CHEBI:24400
)
bacillithiol (
CHEBI:61338
)
is a
monosaccharide derivative (
CHEBI:63367
)
bacillithiol (
CHEBI:61338
)
is a
thiol (
CHEBI:29256
)
bacillithiol (
CHEBI:61338
)
is conjugate acid of
bacillithiol(1−) (
CHEBI:64876
)
Incoming
bacillithiol(1−) (
CHEBI:64876
)
is conjugate base of
bacillithiol (
CHEBI:61338
)
IUPAC Name
(2
S
)-
2-
{[2-
(
L
-
cysteinylamino)-
2-
deoxy-
α-
D
-
glucopyranosyl]oxy}butanedioic acid
Synonyms
Sources
BSH
ChEBI
Cys-GlcN-mal
ChEBI
Manual Xrefs
Databases
Bacillithiol
Wikipedia
CPD8J2-3
MetaCyc
View more database links
Citations
Types
Sources
19578333
PubMed citation
Europe PMC
20308541
PubMed citation
SUBMITTER
20712413
PubMed citation
Europe PMC
21751306
PubMed citation
Europe PMC
22262099
PubMed citation
Europe PMC
23030527
PubMed citation
Europe PMC
23256780
PubMed citation
Europe PMC
24115506
PubMed citation
Europe PMC
24166956
PubMed citation
Europe PMC
Last Modified
13 January 2014
General Comment
2011-02-22
Appears to participate in the sensing of peroxides by
Bacillus
.